Versatile deacylative cross-coupling of aromatic ketones
Hikaru Nakahara, Ryota Isshiki, Masayuki Kubo, Keiichiro Iizumi, Kei Muto, Junichiro Yamaguchi
Abstract
Transition metal-catalyzed cross-couplings represent the most dependable techniques for linking aryl electrophiles with nucleophiles to synthesize a diverse array of valuable aromatic compounds. Although aromatic ketones are crucial intermediates in the synthesis of aromatic compounds with numerous known methods for carbonyl transformations and aromatic ring modifications, few consider them as aryl electrophiles suitable for cross-coupling. This is primarily because forming new bonds with nucleophiles requires the cleavage of a strong C–C bond. Herein, we introduce a cross-coupling method that effectively utilizes aromatic ketones as versatile aryl electrophiles. The cornerstone of our strategy is the transformation of aromatic ketones into aromatic esters via sequential Claisen and regioselective retro-Claisen condensations. The resulting esters are then capable of undergoing reactions with various nucleophiles in a one-pot process.